Alfbed pongbatz



Patented I Nov. 20, 1928.

UNITED STATES-PATENT OFFlCE.

ALFRED ronena'rz,

or can, aus'rnm, ASSIGNOR 'ro rnmcn muss, or GENOA, ITALY.

MANUFACTURE OI CYANIDES OF THE PEBYLENE SERIES.

Ho Drawing. Application filed June 18,

3.10 dicyanide of perylene has been pre- Example -I. A 1 part by weight of dichloro perylene is intimately mixed with 1 part by weight of cuprous cyanide and the mixture is heated 2 to 300 centigrade. At this temperature it is molten and very fluid. In thecourse of stirring the mass becomes thicker and finally forms a tough paste whichoccurs after about an hours heating. On cooling down the mass 1 5 becomes solid and brittle.

The product is finelyground and repeatedly treated with aqueous ammonia for removing the major part of the copper. Then the mass is dissolved v :0 solution is filtered oil and permitted to crys- .tallize. The dicyanlde crystallizes "out in brownish red needles, shows no fusion pointup to 350 Centigrade and dissolves in concentrated sul huric acid in the cold with a brown color; on eatingthe color changes into rose. The compound is little soluble in solvents having a low boiling oint, but the solutions show a marked green having a higher boiling point his readily soluble in the heat.

Example II.

1 part by weight of dichloro per lene and isolvents having a mixture has become in hot nitrobenzene, the

compound is a dlchlorodinitril perylene. In

uorescence, in solvents 928," Serial No. 116.943, and in Austria Jane 28, 1925.

is removed by suction from the crystalline product of reaction, which is thoroughly shaken with aqueousammonia and recrystallized from nitrobenzene. The product Iconsists'in the main of monochloroperylenenitril and fuses at 316 centigrade. The compound is little soluble in solvents having a comparatively low boiling point, is easily soluble in dissolves in concentrated sulphuric acid in the cold with a blue color.

Ewample II I 1 part-of tetrachloro-perylene is intimately mixed with-2 parts of cuprous cyanide and to the mixture just so much quinoline is addedthat it becomes pasty. The whole is gradually heated in an air bath with reflux to the boiling temperature dark brown the heating is stopped. g

After cooling the paste is freed from quinoline either by suction or by means of dilute hydrochloric acid. In any case the nitril thus obtained which is contaminated with igher boiling poiiit and of quinoline. After the copper salts is treated for 24 hours with aque-' ous ammonia. The nitril thus purified crystallizes in dark brown needles.

According to the results of analysis this solvents having a low boiling point it is scarcely soluble, in concentrated sulphuric acid it dissolves with a reddish brown color and olive green fluorescence. readily soluble in solvents having a higher boiling point such asnitrobenzene, or quinoline from which it can be obtained in crystals.

.- Ewample IV.

1 part of dibromo-perylene is intimately mixed with 0.5 to 1 part of cuprous cyanide and is heated for several hours, preparatory It is more to the maximum temperature of 300 centigrade with 10 to 20 parts of peridine. When the reaction iscompleted the mass is diluted with water and aqueous ammonia is added into a nibril.

thereto and left to settle for 24 hours; The brown raw-product ma be purified to rystallization from nitro pound thus obtainedis identical as to all of Instead ofdibromoperylene also dichloroperylene may be converted in the same way In this example, the reaction must take place in a closed vessel owing to the pressure of the pyridine vapor at the high temperatures'used, but such increased pressure is not essential for the reaction. I

. As solvents tertiary cyclic bases liquid at roomtemperature, such as pyridine and quinoline are used.

What I claim is:

1; A process for manufacturing cyanides of the perylene -series consisting in mixing halogen compounds of perylene with metal cyanides and heating the mixture to 300 centigrade. A

2. A process of manufacturing cyanides of nzene. The com-- omen ouch properties with its .Example I. a v

The following equation shows thenature of the'reaction in a typical example the product obtained in the perylene series consisting in mixing halogen compounds of perylene'with metal cya-' signaturei i AIZFRED PDNGRATZ. 

